Oakland Vacations from $288
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $374, price is now $288 per person
$288
per person
Feb 11 - Feb 13
just found
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
Room was small and crowded. We were put into two different rooms and neither had a working TV.
Reviewed on Jan 5, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $462, price is now $388 per person
$388
per person
Feb 11 - Feb 13
just found
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Extremely helpful front desk staff facilitated early check in, allowing us to rest prior to event
Reviewed on Dec 27, 2025
The Landing Hotel at Rivers Casino
North Side
Price was $420, price is now $356 per person
$356
per person
Feb 11 - Feb 13
just found
Roundtrip non-stop flight included
Houston (HOU) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,211 reviews)
Great experience! Awesome weekend in Pittsburgh and staying here made getting to the Steelers game so easy!
Reviewed on Jan 5, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Jan 20 to Jan 21
$139 total
Jan 20 - Jan 21
Total with taxes and fees
8.8/10 Excellent! (565 reviews)
Great
Reviewed on Dec 29, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Jan 18 to Jan 19
$214 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (732 reviews)
Perfect room. Great location. Clean and spacious
Reviewed on Jan 3, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$118 nightly
The price is $135 total per night from Jan 19 to Jan 20
$135 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great staff, beautiful hotel. If you prefer quiet, river view rooms are the way to go. Also rooms feel a little dark but it has modern, clean decor. Overall I would definitely stay here again
Reviewed on Dec 24, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$97
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.